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Search results; 305 homes in Chestertown

Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 private bathrooms
26–31 Aug
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4.91 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
18–23 Aug
4.97 out of 5 average rating, 286 reviews
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 251 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.98 out of 5 average rating, 86 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.99 out of 5 average rating, 138 reviews
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
4.98 out of 5 average rating, 200 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 149 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
1–6 Sept
4.87 out of 5 average rating, 195 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 112 reviews
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 187 reviews
Guest house in Chestertown
Private 1 bedroom with access to pool and backyard
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
New place to stay
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
4.98 out of 5 average rating, 66 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
15–20 Aug
4.98 out of 5 average rating, 183 reviews
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 124 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 96 reviews
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Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
17–22 Aug
4.96 out of 5 average rating, 139 reviews
Guest house in Chestertown
Casa Cannon
5 bedrooms, 5 beds, 2 bathrooms
1–6 Aug